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Pineapple Upside Down Cupcakes

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Pineapple Upside Down Cupcakes: Tender vanilla cake topped with a rich caramel sauce and  juicy fruit.  If you like the cake you'll go crazy over the cupcakes!

a closeup of a mini pineapple upside down cake with a ring of pineapple and a cherry on top.

If you like pineapple you may also enjoy my Pina Colada Poke Cake and Pineapple Margaritas

Pineapple upside down cake is one of those recipes that is just a classic. My Grandma made it often when I was growing up.

Sometimes, instead of making a full-sized pcake, I like to make pineapple upside down cake cupcakes. These are mine versions of the classic. All that great flavor, but easier and quicker to make. Plus you don't have to worry about flipping a huge cake over!

Making mini pineapple upside down cakes is great for a crowd. People will love having their own little dessert! Great for potlucks and birthdays too. No one will ever guess how easy they are! For an extra special treat serve with whipped cream, or vanilla ice cream.

a pineapple upside down cupcake on a white plate with a whole pineapple in the background.

What Is Pineapple Upside Down Cake?

Pineapple upside down cake starts with a fluffy vanilla cake batter. On the bottom of the cake pan butter, brown sugar, cherries, and of course pineapple are added. Then the cake batter is added on top. Once the cake is baked and cooled, it is turned out of the pan so that the pineapple and cherry are on top. It is called upside down cake as you are baking the top of the cake on the bottom of the pan. a mini pineapple upside down cake cut in half and topped with pineapple.

Ingredient Notes

Homemade Cakes:

  • Flour, Baking  Powder ,and Salt
  • White Sugar
  • Butter
  • Vanilla
  • Egg
  • Milk: Use whole milk for the best results.

For the Topping

  • Pineapple Slices: Be sure to drain these in a strainer. You could also use fresh pineapple if you prefer.
  • Maraschino Cherries
  • Brown Sugar
  • Butter

mini pineapple upside down cake

How To Make Mini Pineapple Upside Down Cakes

  1. Prep Work: Preheat oven to 350 degrees F. Spray muffin tins with non stick baking spray.
  2. For the Topping: In a medium bowl, combine melted butter and brown sugar. Evenly divide between prepared muffin tins.  Add one pineapple slice and a cherry to each as well.
  3. Dry Ingredients:  In a large bowl, combine flour, salt, and baking powder.
  4. Cream Butter: In another large bowl, cream butter and sugar until light and fluffy. Add in vanilla and eggs.
  5. Alternate flour mixture and milk until everything is just combined.
  6. Bake: Evenly divide between muffin wells. Bake for 18-22 minutes. Cool and flip over to remove.

a mini pineapple upside down cake topped with pineapple and a maraschino cherry with a whole pineapple in the background.

Frequently Asked Questions

Can You Freeze Them?

Yes, you can freeze these cupcakes. In order to freeze these treats, first freeze them individually and uncovered for an hour. Then, wrap each mini cake and freeze. Don't skip freezing them individually first, or the yummy topping could get stuck to the plastic wrap. Thaw in the fridge before enjoying.

Storage

I store them in the fridge to keep the fruit fresh.  Store in a sealed container for up to 3-5 days.

Can You Make Them Ahead?

While this recipe will taste great even if it is made ahead of time, it does not look as nice.  The fruit can sink into the cake or fall off. I suggest making the day of if possible.

More Cupcakes I Love

German Chocolate Cupcakes

Black Forest Cupcakes

Easy Margarita Cupcakes

Hi Hat Cupcakes

📖 Recipe

pineapple upside down cupcakes

Pineapple Upside Down Cupcakes

Tender vanilla cake topped with a rich caramel sauce and  juicy fruit.  If you like the cake you'll go crazy over the cupcakes!
5 from 9 votes
Print Pin Rate
Course: Dessert
Cuisine: American
Prep Time: 15 minutes
Cook Time: 18 minutes
Total Time: 33 minutes
Servings: 12 Cupcakes
Calories: 410kcal

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Ingredients

For the Topping

  • 2 20 Ounce Cans Pineapple Slices
  • 1 Jar Maraschino Cherries
  • Cup Brown Sugar Packed
  • 4 Tablespoons Butter Melted

For the Cakes

  • 2 ½ Cups All Purpose Flour
  • 1 ⅓ Cup White Sugar
  • 2 ½ Teaspoons Baking Powder
  • ¼ Teaspoon Salt
  • ¾ Cup Butter Softened
  • 1 Teaspoon Vanilla
  • 3 Eggs
  • 1 ¼ Cups Milk
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Instructions

  • Preheat oven to 350 degrees F. Spray a standard size muffin tin with non stick baking spray. 
  • In a medium bowl, combine brown sugar and melted butter. Divide between muffin tins. Also, add one pineapple slice and one cherry to each. 
  • In a large bowl, combine flour, salt, and baking powder. 
  • In another large bowl, cream butter and sugar until light and fluffy. Add vanilla, and eggs one at a time. 
  • Alternate adding in flour mixture and milk until everything is just combined.  
  • Divide evenly between prepared pans.  Bake for 18-22 minutes. 
  • Cool before flipping over. 

Nutrition

Calories: 410kcal | Carbohydrates: 61g | Protein: 5g | Fat: 16g | Saturated Fat: 10g | Cholesterol: 81mg | Sodium: 214mg | Potassium: 186mg | Fiber: 1g | Sugar: 40g | Vitamin A: 590IU | Calcium: 99mg | Iron: 1.6mg
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10 Comments

  1. 5 stars
    Since no size of muffin pan was mentioned, I used a standard muffin pan and found that 1/2 of the recipe made 12 cupcakes. Which is good, because the 4 of us demolished them. So good!

  2. 5 stars
    Thank you so much for this pineapple upside down cupcakes recipe! This is very easy to make and really delicious! Will surely make this again! Well done!

  3. 5 stars
    Was at the Mexican market this morning and saw some pineapple upside down cupcakes! Thought they looked amazing but decided to not buy them but make them instead! Perfect timing with this recipe! One of my favorite cakes and I LOVE it in cupcake size! Moist, delicious, and a little bit caramelized. I'm not sure how I could possibly love this more! 🙂

  4. 5 stars
    Every time my daughter and I make pineapple upside down cake, we always fail, but with your recipe ours turned out perfect and so delicious! So yummy. Can’t wait to make this again!